Assembly of 5 H-dibenzo[ a, d]cycloheptenes by a formal [5 + 2] annulation of ortho-aryl alkynyl benzyl alcohols with arenes

Zhebing Zhang; Tao Cai; Zhaohui Zhan; Huiting Xu; Lemao Yu; Xiang Luo; Chunmei Li; Yuzhen Gao; Xuemei Wei; Xinzhi Chen; Runpu Shen

doi:10.1039/d2ob01335e

Assembly of 5 H-dibenzo[ a, d]cycloheptenes by a formal [5 + 2] annulation of ortho-aryl alkynyl benzyl alcohols with arenes

Org Biomol Chem. 2022 Sep 21;20(36):7221-7225. doi: 10.1039/d2ob01335e.

Authors

Zhebing Zhang¹, Tao Cai^{1

2

3}, Zhaohui Zhan¹, Huiting Xu¹, Lemao Yu¹, Xiang Luo¹, Chunmei Li¹, Yuzhen Gao⁴, Xuemei Wei¹, Xinzhi Chen³, Runpu Shen^{1

2}

Affiliations

¹ College of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing, 312000, China. cait361@usx.edu.cn.
² Zhejiang Engineering Research Center of Fat-Soluble Vitamin, China. srunpu@usx.edu.cn.
³ College of Chemical and Biological Engineering, Zhejiang University, Hangzhou, 310027, China. xzchen@zju.edu.cn.
⁴ Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.

PMID: 36053155
DOI: 10.1039/d2ob01335e

Abstract

A new synthetic methodology for the synthesis of 5H-dibenzo[a,d]cycloheptenes from ortho-aryl alkynyl benzyl alcohols and arenes via a Tf₂O-mediated formal [5 + 2] annulation reaction has been achieved. From this transformation, structurally diverse 5H-dibenzo[a,d]cycloheptenes were achieved in moderate to good yields. This transformation probably involves an intermolecular Friedel-Crafts-type alkylation and a subsequent intramolecular 7-endo-dig cyclization in one pot, highlighting the high efficiency, regioselectivity, and step-economy of this protocol.